1. It depends. If you itemize deductions and those combined are more than the standard deduction you can otherwise it doesn’t really make sense to. This does a decent job of explaining: https://www.investopedia.com/are-health-insurance-premiums-t...

2. I believe it does and I can’t answer the other question with any confidence. Insurance was a big reason my mother kept her job which covered us as a family when my dad started his own business even though she was basically working two jobs because she was also helping with the new business after work.